Systems Engineer - Microsoft

Location: Chicago, United States; participation in a global support team, on-call rotation, and occasional weekend maintenance required.

Salary: $120,000–$160,000 annual base salary, depending on experience, qualifications, and relevant skills. Annual discretionary bonus is also available.

Company

Diversified trading firm operating across global financial markets and expanding into real estate, venture capital, and cryptoassets.

What you will do

• Administer Active Directory, DNS, DHCP, Group Policy, and Exchange across on-premise, online, and hybrid environments.
• Deploy, maintain, and support Windows Server environments from 2016 through 2025.
• Support Entra ID, OneDrive, Copilot, and Microsoft 365 cloud services.
• Configure single sign-on and federation using SAML, OAuth/OIDC, and SCIM.
• Resolve operations queue tickets, respond to critical production incidents, and implement infrastructure changes through firmwide change-management processes.
• Document systems, create repeatable runbooks, and participate in global support, on-call, and weekend maintenance activities.

Requirements

• Experience managing Windows Server infrastructure in high-visibility, mission-critical environments.
• Administration experience with Active Directory, Group Policy, DNS, DHCP, and Failover Clustering.
• Experience with Entra ID, Exchange Server/Online/Hybrid, and MECM/SCCM is preferred.
• Ability to use PowerShell or Python to automate routine administrative tasks.
• Knowledge of networking fundamentals, server hardware, and virtual machine deployments.
• Strong written and verbal communication skills, with the ability to collaborate across teams and resolve technical and operational issues.

Nice to have

• Experience with Splunk, Grafana, Alertmanager, or Prometheus.
• Familiarity with DevOps, CI/CD, infrastructure as code, containerization, or Kubernetes.
• Previous experience in trading or financial services.

Culture & Benefits

• Autonomous environment focused on automation, curiosity, practical solutions, and exceptional support for trading and operational teams.
• Global support collaboration with on-call rotation and occasional weekend maintenance.
• Medical, pharmacy, dental, and vision insurance.
• 401(k) with discretionary employer match, disability and life insurance, health savings accounts, and flexible spending accounts.